Tenuazonic acid-(Copper salt)

Names

[ CAS No. ]:
610-88-8

[ Name ]:
Tenuazonic acid-(Copper salt)

[Synonym ]:
3-acetyl-5-(butan-2-yl)-4-hydroxy-1,5-dihydro-2H-pyrrol-2-one
3-Acetyl-5-sec-butyl-4-hydroxy-1,5-dihydro-2H-pyrrol-2-one
4-acetyl-2-butan-2-yl-3-hydroxy-1,2-dihydropyrrol-5-one
2H-Pyrrol-2-one, 3-acetyl-1,5-dihydro-4-hydroxy-5-(1-methylpropyl)-

Biological Activity

[Description]:

Tenuazonic acid, belonging to tetramic acids that are the largest family of natural products, is a putative nonhost-selective mycotoxin isolated from Alternaria alternate[1]. Tenuazonic acid blocks electron transport beyond primary quinone acceptor (QA) by interacting with D1 protein and it is a broad-spectrum and effective photosystem II (PSII) inhibitor[2].

[Related Catalog]:

Research Areas >> Others

Signaling Pathways >> Others >> Others

[Target]

PSII[2]

[References]

[1]. Zhou B, et al. An evaluation of tenuazonic acid, a potential biobased herbicide in cotton. Pest Manag Sci. 2019 Mar 7.

[2]. Chen S, et al. Recent advances in tenuazonic acid as a potential herbicide. Pestic Biochem Physiol. 2017 Nov;143:252-257.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
401.1±45.0 °C at 760 mmHg

[ Melting Point ]:
74.5°C

[ Molecular Formula ]:
C₁₀H₁₅NO₃

[ Molecular Weight ]:
197.231

[ Flash Point ]:
196.4±28.7 °C

[ Exact Mass ]:
197.105194

[ PSA ]:
66.40000

[ LogP ]:
0.81

[ Vapour Pressure ]:
0.0±2.1 mmHg at 25°C

[ Index of Refraction ]:
1.519

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UY7425000

CHEMICAL NAME :: 3-Pyrrolin-2-one, 3-acetyl-5-sec-butyl-4-hydroxy-, L-

CAS REGISTRY NUMBER :: 610-88-8

LAST UPDATED :: 199709

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C10-H15-N-O3

MOLECULAR WEIGHT :: 197.26

WISWESSER LINE NOTATION :: T5MV EHJ CV1 DQ EY2&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 225 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 5,65,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 81 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EVHPAZ EHP, Environmental Health Perspectives. (U.S. Government Printing Office, Supt of Documents, Washington, DC 20402) No.1- 1972- Volume(issue)/page/year: 4,87,1973

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 145 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 5,65,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 125 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 5,65,1981

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301

[ Precautionary Statements ]:
P301 + P310

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
22

[ RIDADR ]:
UN 2811 6.1/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
UY7425000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Natural occurrence of four Alternaria mycotoxins in tomato- and citrus-based foods in China.

J. Agric. Food Chem. 63(1) , 343-8, (2015)

A total of 70 tomato-based and 86 citrus-based products collected in China were analyzed for alternariol, alternariol monomethyl ether, tentoxin, and tenuazonic acid by ultraperformance liquid chromat...

Evaluation of analogs of reutericyclin as prospective candidates for treatment of staphylococcal skin infections.

Antimicrob. Agents Chemother. 53 , 4028-31, (2009)

The potential for reutericyclin derivatives to be used as topical antibiotics to treat staphylococcal skin infections was investigated. All reutericyclins inhibited the growth of clinical isolates of ...

Effects of nisin and reutericyclin on resistance of endospores of Clostridium spp. to heat and high pressure.

Food Microbiol. 34(1) , 46-51, (2013)

The effects of high pressure, temperature, and antimicrobial compounds on endospores of Clostridium spp. were examined. Minimal inhibitory concentrations (MIC) of nisin and reutericyclin were determin...